US5181992A - Separation of isomers, e. g., phenethyl bromide from 1-phenyl-1-bromoethane - Google Patents
Separation of isomers, e. g., phenethyl bromide from 1-phenyl-1-bromoethane Download PDFInfo
- Publication number
- US5181992A US5181992A US07/537,926 US53792690A US5181992A US 5181992 A US5181992 A US 5181992A US 53792690 A US53792690 A US 53792690A US 5181992 A US5181992 A US 5181992A
- Authority
- US
- United States
- Prior art keywords
- isomer
- phenyl
- hydrogen
- phenethyl bromide
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000926 separation method Methods 0.000 title claims description 9
- CRRUGYDDEMGVDY-UHFFFAOYSA-N 1-bromoethylbenzene Chemical compound CC(Br)C1=CC=CC=C1 CRRUGYDDEMGVDY-UHFFFAOYSA-N 0.000 title abstract description 11
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims abstract description 7
- 239000008096 xylene Substances 0.000 claims abstract description 7
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001491 aromatic compounds Chemical group 0.000 claims abstract 2
- 230000005494 condensation Effects 0.000 claims abstract 2
- 238000009833 condensation Methods 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- -1 alkyl radical Chemical class 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 10
- 238000006482 condensation reaction Methods 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000008378 aryl ethers Chemical class 0.000 claims description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 101150108015 STR6 gene Proteins 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 18
- GNPWYHFXSMINJQ-UHFFFAOYSA-N 1,2-dimethyl-3-(1-phenylethyl)benzene Chemical compound C=1C=CC(C)=C(C)C=1C(C)C1=CC=CC=C1 GNPWYHFXSMINJQ-UHFFFAOYSA-N 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000004821 distillation Methods 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- SHKKTLSDGJRCTR-UHFFFAOYSA-N 1,2-dibromoethylbenzene Chemical compound BrCC(Br)C1=CC=CC=C1 SHKKTLSDGJRCTR-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003738 xylenes Chemical class 0.000 description 3
- GTLWADFFABIGAE-UHFFFAOYSA-N 1-chloroethylbenzene Chemical compound CC(Cl)C1=CC=CC=C1 GTLWADFFABIGAE-UHFFFAOYSA-N 0.000 description 2
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010408 sweeping Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- SQSJCFQHNSGVBW-UHFFFAOYSA-N (1-bromo-4-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(CBr)CCC1=CC=CC=C1 SQSJCFQHNSGVBW-UHFFFAOYSA-N 0.000 description 1
- AOWVXBUUWBOTKP-UHFFFAOYSA-N 1-methyl-2-(1-phenylethyl)benzene Chemical compound C=1C=CC=C(C)C=1C(C)C1=CC=CC=C1 AOWVXBUUWBOTKP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical group COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/395—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification of at least one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S203/00—Distillation: processes, separatory
- Y10S203/06—Reactor-distillation
Definitions
- U.S. Pat. No. 3,058,892 describes treating the mixture of phenethyl bromide and its isomer with zinc oxide at a temperature ranging from 100° C. to 150.C in order to selectively decompose the isomer. It is recommended to minimize the temperature and the reaction time in order to prevent the decomposition of the phenethyl bromide.
- Another object of this invention is the provision of an improved process for the selective separation of a variety of isomeric systems that can be carried out at lower temperatures than the prior art separations.
- the isomers (I) and (II) can comprise a simple admixture thereof, or they can be dissolved in a solvent therefor.
- the Friedel-Crafts catalyst is known, per se. The following are termed Friedel-Crafts catalysts: Lewis acids (metal halides, etc.), protonic acids and zeolites. Exemplary of the metal halides, ferric chloride and aluminum chloride are representative. Exemplary protonic acids include the oxyacids such as sulfuric acid and paratoluenesulfonic acid. And exemplary zeolites include the decationized X or Y faujasites.
- the temperature can also vary over wide limits; advantageously, it is within a temperature range in which the isomers and the compound with which the condensation reaction is carried out are liquid. It is preferred to carry out the reaction at a temperature ranging from 50° to 100° C. The temperature is also selected such that the condensation reaction can be carried out at atmospheric pressure or at a pressure which does not exceed a few bars.
- step (a) of the subject process i.e., the condensation reaction
- the reaction mixture can be washed with an aqueous solution of hydrochloric acid.
- Step (b) i.e., the separation to recover isomer (II), is then carried out. Any technique can be used therefor, but distillation is the preferred.
- thermometric casing with thermocouple thermocouple
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8907800 | 1989-06-13 | ||
| FR8907800A FR2648130B1 (fr) | 1989-06-13 | 1989-06-13 | Procede de separation de deux isomeres, son application a la purification du phenyl-1 bromo-2 ethane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US5181992A true US5181992A (en) | 1993-01-26 |
Family
ID=9382655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/537,926 Expired - Fee Related US5181992A (en) | 1989-06-13 | 1990-06-13 | Separation of isomers, e. g., phenethyl bromide from 1-phenyl-1-bromoethane |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5181992A (es) |
| EP (1) | EP0403331B1 (es) |
| JP (1) | JP2701226B2 (es) |
| KR (1) | KR920006538B1 (es) |
| CN (1) | CN1024788C (es) |
| AT (1) | ATE87291T1 (es) |
| CA (1) | CA2017650C (es) |
| DE (1) | DE69001154T2 (es) |
| DK (1) | DK0403331T3 (es) |
| ES (1) | ES2054292T3 (es) |
| FI (1) | FI95240C (es) |
| FR (1) | FR2648130B1 (es) |
| IE (1) | IE64625B1 (es) |
| NO (1) | NO173231C (es) |
| PT (1) | PT94357B (es) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637736A (en) * | 1993-08-06 | 1997-06-10 | Sumitomo Chemical Company, Limited | Process for preparing 1-bromoalkylbenzene derivatives and intermediates thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998029373A1 (fr) * | 1996-12-26 | 1998-07-09 | Nippon Zeon Co., Ltd. | φ-BROMOALKYLBENZENES ET PROCEDE DE PREPARATION |
| US6374732B1 (en) * | 2000-06-05 | 2002-04-23 | Frank Perretta | Dampener for use in lithographic presses |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2246762A (en) * | 1934-12-22 | 1941-06-24 | Unichem Chemikalien Handels A | Method for condensation |
| US2746938A (en) * | 1951-05-10 | 1956-05-22 | Bayer Ag | Sulfonated methylbenzene-halogenated hydrocarbon condensation products as cation exchange resins |
| US3058892A (en) * | 1960-11-07 | 1962-10-16 | Du Pont | Separation of beta-bromoethylbenzene from alpha-bromoethylbenzene by distillation |
| US3453339A (en) * | 1967-05-11 | 1969-07-01 | Chevron Res | 1-haloalkyl substituted aromatic hydrocarbons and process for their production |
| US4219652A (en) * | 1975-09-30 | 1980-08-26 | Eli Lilly And Company | N-Methyl and N-phenethyl-cis-decahydroisoquinolines |
| US4321383A (en) * | 1980-11-24 | 1982-03-23 | E. R. Squibb & Sons, Inc. | Heterobicyclo intermediates |
-
1989
- 1989-06-13 FR FR8907800A patent/FR2648130B1/fr not_active Expired - Lifetime
-
1990
- 1990-05-28 CA CA002017650A patent/CA2017650C/fr not_active Expired - Fee Related
- 1990-06-01 DE DE90401490T patent/DE69001154T2/de not_active Expired - Fee Related
- 1990-06-01 AT AT90401490T patent/ATE87291T1/de not_active IP Right Cessation
- 1990-06-01 EP EP90401490A patent/EP0403331B1/fr not_active Expired - Lifetime
- 1990-06-01 ES ES90401490T patent/ES2054292T3/es not_active Expired - Lifetime
- 1990-06-01 DK DK90401490.9T patent/DK0403331T3/da active
- 1990-06-08 KR KR1019900008413A patent/KR920006538B1/ko not_active IP Right Cessation
- 1990-06-12 FI FI902953A patent/FI95240C/fi not_active IP Right Cessation
- 1990-06-12 PT PT94357A patent/PT94357B/pt not_active IP Right Cessation
- 1990-06-12 IE IE211690A patent/IE64625B1/en unknown
- 1990-06-13 US US07/537,926 patent/US5181992A/en not_active Expired - Fee Related
- 1990-06-13 JP JP2154975A patent/JP2701226B2/ja not_active Expired - Lifetime
- 1990-06-13 NO NO902627A patent/NO173231C/no not_active IP Right Cessation
- 1990-06-13 CN CN90104354A patent/CN1024788C/zh not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2246762A (en) * | 1934-12-22 | 1941-06-24 | Unichem Chemikalien Handels A | Method for condensation |
| US2746938A (en) * | 1951-05-10 | 1956-05-22 | Bayer Ag | Sulfonated methylbenzene-halogenated hydrocarbon condensation products as cation exchange resins |
| US3058892A (en) * | 1960-11-07 | 1962-10-16 | Du Pont | Separation of beta-bromoethylbenzene from alpha-bromoethylbenzene by distillation |
| US3453339A (en) * | 1967-05-11 | 1969-07-01 | Chevron Res | 1-haloalkyl substituted aromatic hydrocarbons and process for their production |
| US4219652A (en) * | 1975-09-30 | 1980-08-26 | Eli Lilly And Company | N-Methyl and N-phenethyl-cis-decahydroisoquinolines |
| US4321383A (en) * | 1980-11-24 | 1982-03-23 | E. R. Squibb & Sons, Inc. | Heterobicyclo intermediates |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637736A (en) * | 1993-08-06 | 1997-06-10 | Sumitomo Chemical Company, Limited | Process for preparing 1-bromoalkylbenzene derivatives and intermediates thereof |
| US6063940A (en) * | 1993-08-06 | 2000-05-16 | Sumitomo Chemical Company, Limited | Process for preparing 1-bromoalkylbenzene derivatives and intermediates thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| KR920006538B1 (ko) | 1992-08-08 |
| CN1024788C (zh) | 1994-06-01 |
| IE64625B1 (en) | 1995-08-23 |
| FI902953A0 (fi) | 1990-06-12 |
| FR2648130B1 (fr) | 1991-09-06 |
| DE69001154T2 (de) | 1993-10-14 |
| KR910000584A (ko) | 1991-01-29 |
| NO902627D0 (no) | 1990-06-13 |
| EP0403331A1 (fr) | 1990-12-19 |
| FR2648130A1 (fr) | 1990-12-14 |
| JPH03101629A (ja) | 1991-04-26 |
| ES2054292T3 (es) | 1994-08-01 |
| ATE87291T1 (de) | 1993-04-15 |
| NO902627L (no) | 1990-12-14 |
| NO173231B (no) | 1993-08-09 |
| FI95240C (fi) | 1996-01-10 |
| FI95240B (fi) | 1995-09-29 |
| DK0403331T3 (da) | 1993-04-19 |
| EP0403331B1 (fr) | 1993-03-24 |
| CN1049492A (zh) | 1991-02-27 |
| DE69001154D1 (de) | 1993-04-29 |
| CA2017650A1 (fr) | 1990-12-13 |
| NO173231C (no) | 1993-11-17 |
| PT94357B (pt) | 1997-01-31 |
| IE902116A1 (en) | 1991-01-02 |
| JP2701226B2 (ja) | 1998-01-21 |
| CA2017650C (fr) | 1995-03-21 |
| PT94357A (pt) | 1991-02-08 |
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